Sodium Carbonate → 3-(4,6-Dimethylpyrimidin-2-yl)aniline

HRID 1690671Notes

Reaction equation

HRID 1690671 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH2:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC#N.O>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([C:15]2[CH:16]=[C:11]([NH2:10])[CH:12]=[CH:13][CH:14]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 205502-Chloro-4,6-dimethylpyrimidineHCID 922693-Aminophenylboronic acid

Product 1

HCID 576185003-(4,6-Dimethylpyrimidin-2-yl)aniline

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-Chloro-4,6-dimethyl-pyrimidine (92 mg, 0.645 mmol, 1 eq.), 3-aminobenzene boronic acid (100 mg, 0.645 mmol, 1 eq.), Na2CO3 (137 mg, 1.29 mmol, 2 eq.), and Pd(PPh3)2Cl2 (23 mg, 0.032 mmol. 5 mol %) in a 1:1 v/v mixture of CH3CN/H2O (2.6 mL) is purged with N2 for 5 minutes and then heated in a microwave at 150° C. for 5 minutes. After cooling to room temperature, the reaction is diluted with EtOAc and sequentially washed with saturated aqueous NaHCO3 and saturated aqueous NaCl. The organic solution is dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (1:1 hexanes/EtOAc) to give 3-(4,6-Dimethyl-pyrimidin-2-yl)-phenylamine as a yellow semisolid. [MS: (ES+) 200.1 (M+1)+].

Workup

  1. customis purged with N2 for 5 minutes
  2. temperatureAfter cooling to room temperature
  3. additionthe reaction is diluted with EtOAc
  4. washsequentially washed with saturated aqueous NaHCO3 and saturated aqueous NaCl
  5. dry with materialThe organic solution is dried over Na2SO4
  6. concentrationAfter concentration
  7. customthe residue is purified by silica gel chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-674d4b9b90424ccd9d2c9a2593f10996
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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